Sulphocarboxxtic acid amide



' example without being Patented Oct, 24,

sunrnooaanoxmc A011) AMmE wmma] Hentrich, Erlaugcn,

Keppler, Cologne-on-the-Rhine,

ine s,- by mesne ass and lielmuti Germany, as-

gnments, to I. G. Farbenindustrie Aktiengesellschaft, Frankfort-on-the- Main,Ge

many, a corporation 01' Germany,

' .No Drawing. Application August 3, 1931, Serial 554,942, and in Germany August 5, 1930 7 h 3 Claims, (01.260-124) The present invention relates to; new sulfocarboxylic acid amides being substituted in the amido group by a saturated or unsaturated higher allphatic radical containing. at least 8 carbon atoms.

The new-compounds correspond to the probable general formula: I a

I 10 wherein R stands for a substituted or unsubstitutedalkylene or .aralkylene or, arylene, such as ethylene, propylene, x 0 CH2-"-CHOHCH:, C6H4-'CH2,

CGH3C1'CH2,C6H3NO2, X means hydrogen, ammonium (NHi) or a metallic equivalent, R1 represents a saturated or un-' saturated aliphatic radical containing atieast 8 carbonatoms, R2 means hydrogen,,alk'yl, for instance, a lower alkyl group or the above-men- 2 tionedsaturated or unsaturated alphatic radical containing at least 8 carbon atoms aralkyl, aryl or cycloalkyl.

.The manufacture of these compounds is carried' out'by causing a primary or secondary amine 5 containing at least one higher unsubstituted or substituted aliphatic radical to reactfwith a carboxylicacid containing atleast one sulfonic acid group,or an appropriate functional derivative thereof, for example, ester salts. I

'Thenew compounds are colorless .or weakly colored substances soluble in water or alkalies andaresu'itable as auxiliary products in the textile industry as softening, purifying, frothing, wetting and dispersing agents and .in facilitating 5 even dyeing; The eflicacy of the same is to a large extent independent of the-acid'or. alkaline reaction of, and of salt content in, the washing and refining baths. 7

. Our invention is illustrated by the following limited thereto.- The parts are by weight.

Example-l2 parts of heptadecylamine are heated while stirring to 100-200 C. with 10 parts of the salt of the ethyl ester of sulfoacetic acid until the mass is soluble in hot water.

By crystallizing from 70 to 80% alcohol the reaction product is obtained in the form of white, short, felted needles which do not melt without decomposition. The substance is readily soluble in hot water and rather difilcultly soluble in cold water; the solutions are stableto acids and when employed in conjunction with hard water do not yield insoluble calcium soaps.

Heptadecylamine is preparedfrom stearic acid with the aid of the Curtius reaction (see Holledustry.

" wherein R stands for an alkylene, aralkylene or mann, Lehrbuch der organischen Chemie 1930. page, 292), through the corresponding azide. The product thus obtained is awax-like and color-'- less substance insoluble in water but easily soluble in organic solvents, such as ether, benzene, benzine and alcohol. The heptadecylamine melts at 49 C. (see Berichte der deutschen chemischenyGesellschaft, vol.- 21,

page 2489.) Y We claim: v 1. The new compounds of the probable general wherein R stands-for analkylene-, aralkyleneor arylene-radical which-may be substituted, by a substituent selected from the group consisting of halogen-, hydroxy-, carboxylic-, nitroand 'alkyl groups, X means hydrogen',-ammonium (NHi) or a metallic equivalent, R1 stands for an aliphatic radical which may be substituted ,by' a substituent selected fromth'e groupconsisting of hy-' droxy-, amino-, and halogen groups and which contains at least 8 carbon atoms, R: means hydrogen or a substituent of the group consisting of an alkyl, aralkyl or aryl or cycloalkyl radical, or an aliphatic radical containing at least 8 carbon atoms being colorless or weakly colored substances, soluble in water or, alkalies and being suitable as auxiliary products in the textile in- 2, The compounds of the probable formula:

II JZgr-co-n-sm-x A 1 arylene which. maybe substitutedbya substituent selected from the group'consisting of halogen-, hydroxy-, carboxyli c', nitroand alkyl groups, X means hydrogen, ammonium or a me- -talllc equivalent, and alkyl means an aliphatic radical containing at least 8 carbon atoms, being 7 colorless or weakly colored substances, soluble in water or alkalies and being suitable as auxiliary products in the textile industry.

3. The sodium salt of heptadecylsulfacetamide having the probable formula: Y

CnHawNH-CO-CHa-SOsNii being a colorless water-soluble crystalline substance, stable to acids and to-hardwater and being particularly suitable as softening, purifying, frothing, wetting and dispersing agent.

HENTRICH. HELMIUT, KEPPLER. 

